1053-23-2

Basic information

• Product Name: 1,1',1'',1'''-(1,2-Cyclopropanediylidene)tetrakisbenzene
• Synonyms: 1,1',1'',1'''-(1,2-Cyclopropanediylidene)tetrakisbenzene;1,1',1'',1'''-cyclopropane-1,1,2,2-tetrayltetrabenzene
• CAS NO: 1053-23-2
• Molecular Formula: C₂₇H₂₂
• Molecular Weight: 346.46
• Mol File: 1053-23-2.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,1',1'',1'''-(1,2-Cyclopropanediylidene)tetrakisbenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1',1'',1'''-(1,2-Cyclopropanediylidene)tetrakisbenzene(1053-23-2)
• EPA Substance Registry System: 1,1',1'',1'''-(1,2-Cyclopropanediylidene)tetrakisbenzene(1053-23-2)

Safety Data

• Hazardous Substances Data: 1053-23-2(Hazardous Substances Data)

Usage

Chemical compound

A substance formed from the combination of two or more elements in a fixed proportion by mass.

Tetrakisbenzene core structure

A central structure consisting of four benzene rings.

Cyclopropane moiety

A three-carbon ring structure that links the tetrakisbenzene core.

Rigid structure

The molecule has a stable and inflexible shape due to its chemical bonding.

Planar structure

The molecule is flat, with all atoms lying in the same plane.

Symmetric structure

The molecule has a balanced arrangement of atoms, with mirror-image symmetry.

Organic electronics

A field that involves the use of organic materials in electronic devices.

Organic light-emitting diodes (OLEDs)

Devices that emit light when an electric current is applied, using organic materials.

Organic field-effect transistors (OFETs)

Transistors that use organic materials as the semiconductor layer, enabling flexible and lightweight electronics.

Optoelectronic devices

Devices that involve the interaction of light with electronic components, such as solar cells and photodetectors.

Supramolecular chemistry

The study of non-covalent interactions between molecules, leading to the formation of larger, complex structures.

Molecular recognition

The ability of molecules to selectively bind to specific target molecules, which is crucial for many biological and chemical processes.

Upstream product

• 123-91-1 1,4-dioxane 
• 87156-62-5 1,1,3,3-tetraphenyl-1,3-dimethoxypropane 
• 530-48-3 1,1-Diphenylethylene 
• 2051-90-3 Dichlorodiphenylmethane 
• 91-63-4 2-methylquinoline 
• 611-73-4 Benzoylformic acid 
• 908093-98-1 diazodiphenylmethane 
• 1221-72-3 Bis(p-methoxyphenyl)diazomethan 
• 4545-20-4 benzophenone tosylhydrazone 

Downstream Products

• 4614-01-1 1,1,3-triphenylindene 
• 86477-15-8 3-methoxy-1,1,3,3-tetraphenylpropene 
• 1674-18-6 tetraphenylallene 
• 27674-41-5 1,1,2,2-tetraphenyl-2-propen-1-ol 
• 36171-50-3 1,1,3,3-tetraphenylpropane 
• 35818-87-2 3,3,5,5-tetraphenyl-1,2-dioxolane 
• 119-61-9 benzophenone 
• 947-91-1 Diphenylacetaldehyde 

Relevant articles and documents

Laser-Jet Photochemistry: The Photofragmentation of Triplet 1,1,3,3-Tetraarylpropane-1,3-diyls and Their Role in the Photometathesis between Diarylcarbenes and 1,1-Diarylehylenes

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Visible-Light-Triggered, Metal- and Photocatalyst-Free Acylation of N-Heterocycles

A photoinduced acylation of N-heterocycles is explored. This visible-light triggered reaction occurs not only under extremely mild reaction conditions, but also does not require the presence of a photosensitizer. The mechanistic studies suggest formation of EDA complexes prompt to harness the energy from visible-light. Compatibility with a large panel of α-keto acids as acyl precursors and an array of N-heterocycles clearly showcase the synthetic potential of this handy and green acylation protocol. (Figure presented.).

Mechanism of Dicyanoanthracene-Photosensitized Oxygenation of 1,1,2,2-Tetraarylcyclopropanes and 1,1,3,3-Tetraarylpropenes

1,1,2,2-Tetraphenylcyclopropane (2a) and electron-donor-substituted 1,1-diaryl-2,2-diphenylcyclopropanes 2b-f as well as correspondingly substituted 1,1-diaryl-3,3-diphenylpropenes 5a-e and 3,3-diaryl-1,1-diphenylpropenes 6a-e were irradiated in CCl4 and acetonitrile in the presence of oxygen and various sensitizers.The cyclopropanes as well as the propenes are inert toward singlet oxygen in both solvents.In electron-transfer-induced oxygenation reactions, photosensitized by 9,10-dicyanoanthracene in acetonitrile, cyclopropanes 2d-f, carrying efficient electron-donating 4-methoxyphenyl and 4-phenoxyphenyl groups, yield 1,2-dioxolanes 3d-f exclusively.Cyclopropanes 2b and 2c, which carry less efficient electron-donating 4-methylphenyl groups, give rise to dioxolanes 3b and 3c, respectively, as major products.In addition, allylic hydroperoxides 4b and 4c are formed, which are further oxygenated to benzophenone (10) and the corresponding diaryl ketones 7b and 7c. 1,1,2,2-Tetraphenylcyclopropane (2a) yields dioxolane 3a and allylic hydroperoxide 4a in a ratio of 3:2 as major products; in addition, 1,1,3,3-tetraphenylpropene (5a=6a) is formed as a minor product that is oxygenated under the reaction conditions to benzophenone (10) and diphenylacetaldehyde (8).By use of biphenyl (co-sensitizer), lithium perchlorate (special salt effect), and p-benzoquinone (quencher of O2.-), it is shown that cyclopropanes 2a-f are oxygenated in chain reactions involving (1) 1,3-radical cations 2.+ rather than 1,3-triplet biradicals and (2) triplet ground-state oxygen rather than the superoxide radical anion.Use of 1,8-dihydroxyanthraquinone as a sensitizer supports these results.Propenes 5a-e and 6a-e yield ketones and aldehydes as major products by reactions of 1,2-radical cations 5.+ and 6.+ with O2.- as the oxygenating species.Dioxolanes and allylic hydroperoxides are not produced from these propenes.A mechanism is developed for the electron-transfer-induced photooxygenation of 1,1,2,2-tetraarylcyclopropanes 2 that shows that the increase of the resonance stabilization of the 1,3-radical cation 2.+, caused by substitution of phenyl groups by electron-releasing aryl groups and demonstrated by the concomitantly decreasing oxidation potential of 2, plays the essential role in determining oxygenation rates and product formation.